Technical investigations define this Escalation Engineer role at Island, using networking, web debugging, and log analysis across enterprise environments.
As part of Island’s global Escalation team, you will connect customers with engineering teams through complex technical investigations. You will analyze browser, network, cloud, and endpoint layers while translating findings for enterprise customers. Your work will also identify systemic improvements and inform product priorities.
Key Responsibilities: Own escalated investigations from triage through root cause and resolution
Analyze Chromium traces, network captures, logs, and diagnostic tools
Write evidence-based reports with reproduction steps, logs, and traces




Communicate technical findings clearly throughout customer escalations
Contribute to runbooks, knowledge articles, and incident analysis
Requirements: Five or more years in technical support escalation
Knowledge of TCP/IP, DNS, TLS/SSL, proxies, and VPNs
Web debugging experience with developer tools and network traces
Experience querying logs, traces, and metrics in observability platforms
Knowledge of Windows or mac OS and enterprise endpoint management
Apply technical investigation, customer communication, and cross-team escalation skills to shape Island’s enterprise product experience.

📌 Senior technical escalation engineer (Toronto)
🏢 Island
📍 Toronto